In the coin control list mode I'm getting estimates of between 50-64 days for individual matured blocks to stake,while on the syncing wheel at the front of the wallet console, I'm getting 3-5 days and 2-4 days to staking.
The second bit takes into account every block you have. As an example that may be easier to grasp, imagine you have a dice, and you roll it till you get a 1. You have 1/6 chance to get 1 at each roll. The expected number of rolls till you get 1 is.... hmmm. a few. You will likely need to roll a few times to get a 1. You might get a 1 on the first roll, and you might need to roll 10 times before getting one if you're not lucky.
Now, picture a HYP block being such a dice, rolling every second. And now imagine you've got 100 dice. And think about if you roll these 100 dice at once, what is the expected number of whole rolls to get at least a 1 ? It's pretty likely you'll get at least a 1 in that first mass roll.
That's why you get an overall expected time to stake that's a lot lower than the typical time to stake for a single block. The more blocks you have, the larger the gap.